Dimethylformamide → Octyl 4'-hydroxy-4-biphenylcarboxylate

HRID 442597

Reaction equation

HRID 442597 reaction equation
FC(F)(F)[CH:3]([OH:10])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].CN(C)[CH:15]=[O:16].[CH2:18](N(CC)CC)[CH3:19].[CH:25]1[C:34]2[C:29](=[CH:30][C:31]([C:35](Cl)=[O:36])=[CH:32][CH:33]=2)C=C[C:26]=1[C:38](Cl)=O.[CH2:41](Cl)Cl>>[CH2:3]([O:10][C:35]([C:31]1[CH:32]=[CH:33][C:34]([C:25]2[CH:26]=[CH:38][C:15]([OH:16])=[CH:19][CH:18]=2)=[CH:29][CH:30]=1)=[O:36])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:41]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 978042-Octanol, 1,1,1-trifluoro-HCID 34855962,6-Naphthalenedicarbonyl dichloride

Product 1

HCID 14692993Octyl 4'-hydroxy-4-biphenylcarboxylate

Procedure

Optically active 1,1,1-trifluoro-2-octanol (0.3 g), dimethylformamide (0.2 g) and triethylamine (0.18 g) were dissolved in methylene chloride (20 ml). To this solution was added in small portions a solution of 2,6-naphthalenedicarboxylic acid dichloride (0.8 g) obtained in the step 2) of Example 7 in methylene chloride (50 ml) under ice-cooling, and the mixture was stirred for about 20 hours. Next, 4-n-octyloxycarbonyl-4'-hydroxybiphenyl (0.55 g) obtained in the step 1) was dissolved in methylene chloride (30 ml) and added in small portions to the reaction mixture. The resulting mixture was stirred for about 20 hours.

Workup

  1. temperaturecooling

Sources & evidence

ORD record
ord-401bdc46047c4f3aa69c17a8d3cd0a1a
Source dataset
uspto-grants-1999_04
Patent number
US05891359

Linked notes

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